


The Wingman

by BabysNotaProp (SuzetteB)



Category: Supernatural
Genre: Alternate Universe - Bar/Pub, Blow Jobs, Businessman Castiel, Come Eating, Come Marking, Destiel Promptober, Hand Jobs, Kissing, M/M, Oral Sex, Promptober, Promptober 2018, Smut, Wingman Dean Winchester
Language: English
Status: Completed
Published: 2018-10-18
Updated: 2018-10-18
Packaged: 2019-08-03 21:17:15
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 1,538
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/16333631
Author URL: https://archiveofourown.org/users/SuzetteB/pseuds/BabysNotaProp
Summary: Dean Winchester’s latest client, Meg Masters, wants to hook up with a sexy businessman named Castiel Novak. As Cas and Dean converse in a local bar, the night takes an unexpected turn.





	The Wingman

**Author's Note:**

> Today’s prompt was “wing”, and I’m pretty sure I went way out in left field but I blame the voice in my head that gives me ideas for crazy shit like this at the most inopportune times. Enjoy!

Dean Winchester: contracted wingman. Hey, it’s America. You can market anything. Throughout the years, hundreds of couples had benefited from his black market-style services. Usually, they found him; he listened to their story and supplied an elaborate plan of action; he got his customer laid; he got paid.

 

Both women and men hired him, but tonight it would be a little spitfire named Meg, pining after the elusive Castiel Novak. This much Dean knew, just from their short meeting: Meg wouldn’t stand a chance without Dean’s special skill set, and this Novak fellow was the yummiest piece of ass Dean ever had the pleasure of meeting.

 

Focus, Dean. Don’t think about those eyes so blue you could drown in them. Don’t think of the thick neck and biceps straining his collared shirt. Don’t think about how his tongue glides across his perfect lips. Fool, don’t do it.

 

“You must be a very busy man,” Dean said as he forced his eyes back up to the man’s eyes. “You own three property management offices, run a charity on the side, and still find time for your niece?”

 

“Yes, well,” Mr. Novak shrugged easily. “It comes at the cost of a social life.”

 

“You’re here now, aren’t you?”

 

Just when Dean thought those lips couldn’t get any more beautiful, they turned up in a smile and Dean felt a blush wash over him for thinking these things about a client’s soon-to-be date.

 

“So uh, Mr. Novak —”

 

“Castiel, please.”

 

Dean smiled, the elegant name rumbling through his head like a thunderstorm. “The charity you mentioned, about the children’s hospital? I know a lady who volunteered there over the summer. Does the name Meg Masters ring a bell?”

 

Castiel tapped his glass idly for a moment. “I’m afraid not. There are so many volunteers coming and going, and most of the times I visit are when only the regulars are working.”

 

“Of course,” Dean nodded politely. “She’s a fine young lady, though. You should meet her.”

 

Eyes darting down, Castiel cleared his throat and thumbed the condensation on his drink. “I’m not sure she’s my type.”

 

Of course, Dean had a response for every “no” in the book. The words laid pressing against his tongue on the back of his teeth, but he couldn’t help but stare at the fascinating man before him. He was so hard working and kind. His black hair begged to be messed up, his jaw kissed and lap sat on. Dean could do the job as well as anyone else but this was business. He needed to pull it together.

 

“She’s gorgeous, feisty, smart,” Dean listed. “That don’t sound like your type?”

 

Castiel looked directly into Dean’s eyes. “She’s a woman.”

 

The smug grin fell off of Dean’s face. How could he have missed it? In his entire file, he hadn’t collected a single picture of Novak with a chick. He wanted to kick himself for not noticing.

 

But there was something else. Mr. Novak’s eyes glazed over with something darker. Something hungry and primal and wild. That glint awoke a fire deep in Dean’s gut, and he felt himself inappropriately aroused right there at the bar.

 

“Uh, I uh,” Dean stammered. “She uh…”

 

It was Castiel’s turn to turn smug. “You, however…”

 

Dean’s eyes shot up. No, this wasn’t supposed to happen. He was supposed to help Meg get laid. She was paying him to get this guy in bed with her. And here he was, flustered and faltering and being flirted with by the object of his client’s affection. It felt backwards and dirty and… kind of sexy.

 

“You, Mr. Winchester…”

 

“Dean,” he interjected, trying his best to appear confident and unruffled. “Call me Dean.”

 

Cas leaned forward in his bar stool and clasped onto Dean’s knee. Dean’s breathing stopped. Castiel’s fingers were thick and strong, and Dean gulped down a lump in his throat thinking about how they’d feel around his cock.

 

“Dean,” Castiel said with a raised brow. “Meet me in my apartment upstairs.”

 

Sliding out of his seat, Dean nodded and tittered something incoherent. He backed out of the bar, not taking his eyes off of the man whose electric touch he could still feel on his leg. He staggered into the restroom, where he sent Meg a mostly misspelled text that the night hadn’t gone to plan but that he’d touch base with her in the morning with a new strategy.

 

His heart hammered in his chest as he awaited Castiel Novak to answer his knock. As soon as the door opened, the mysterious businessman dragged his hand across Dean’s chest and invited him in with a mere look. Castiel pinned him against the door and Dean braced himself to be taken right then, and thank every lucky star for it, but instead Castiel made a declaration.

 

“Meg was never your client, Dean Winchester. I was hers. I’ve wanted you from the very beginning of your career, but I’ve seen clients try to woo you. It’s impossible to unwing the wingman. So I hired my own. And now I have you.”

 

Dean snapped his mouth back shut after he realized it had fallen open. “You hired someone to match me up with you?”

 

Castiel nodded earnestly. “I understand if you don’t want this, after hearing this information.”

 

“Are you kidding?” Dean laughed. “I got into this business because shit like that’s sexy as fuck. I never thought anyone would be able to out-me, me.”

 

Novak narrowed his eyes, his own desire stirred by Dean’s consent. In one fluid motion, he pressed his whole body against Dean and grabbed both sides of his face. Their mouths latched onto each other impatiently, teeth scraping and breath panting. Castiel plunged his tongue into Dean’s mouth, to which he responded with a maddening groan.

 

The kisses were wet and messy, ending with clothes strewn on the floor and cocks brushing each other on the couch. Castiel — or Cas, as Dean decided to call him — held both of their members in those large, strong fingers, squeezing them up and down as Dean twitched in ecstasy below.

 

A bead of precome trickled out of Dean’s slit, and Cas paused from his double handjob to suck it off, eliciting an excited shout from Dean. Taking their cocks in his hands once again, Cas smashed his lips onto Dean’s, giving him a taste of himself.

 

Dean revelled in the feeling of those lips. On his mouth, on his neck, on his cock; they were beautiful wherever he was blessed to have Cas place them. He let out a little whine when Cas pulled away from the kiss, but the anguish was short-lived.

 

“Need more,” Castiel’s rough voice grumbled as he moved between Dean’s legs. “Need to taste you more.”

 

Dean hardly had time to respond before Cas guided his entire length into his mouth. All of it. He could feel his tip grazing Cas’ throat and in reply, Dean whimpered tiny praises over and over. The only thing he could focus on, the only thing that mattered, was this. He looked down to see those gorgeous lips wrapped around the base of his cock, nose brushing against his pelvis.

 

He grabbed onto Cas’ hair, finally giving it the sex makeover it needed. “Cas, get off, I’m gonna… I’m… Cas!”

 

Not one moment too soon, Cas pulled off and held Dean’s cock as come spurted across his swollen lips and dark hair. Dean watched with wide eyes as he painted Castiel with his spend, hoping to remember the sight forever. He pulled himself up, still hazy from the afterglow, and pushed Cas onto his back, hands running drying come through Cas’ thick locks.

 

Cas’ hair dripped with Dean’s spend and stuck out in every which way. His face was covered in it and his blue eyes pierced through Dean with a spark that only heightened the tension between them. He lowered himself slowly onto Cas’ cock, tongue swirling under the head and fingers gently fondling his balls.

 

Cas grunted in approval and held Dean’s head steady as he fucked his mouth, his thrusts short and fast. Dean held onto Cas’ hips as tears streamed down his face. Cas gasped in warning of his orgasm, and Dean swallowed around his cock to give push him over the edge.

 

As Cas came down his throat, Dean moaned at the welcomed taste and thought about what a wild fantasy he had just lived. He had been besotted with Mr. Novak ever since he built his file, and now here he was, all his. Not only that, but Cas had wanted him just as much.

 

The two laid naked and covered in semen as Cas flipped through TV channels. His hair was sexier than words could describe, but they should probably clean up. Dean sadly thought about their night coming to an end.

 

“Hey Cas?”

 

“Hmm.”

 

“You uh,” Dean paused. Being the one to initiate dates and nothing beyond that, he wasn’t sure how to handle the after-the-fact. “You wanna do this again sometime?”

 

“Mr. Winchester, you could at least offer to buy me dinner first.”

 

Dean lit up. “You wanna go on a date?”

 

Cas smiled. “What a marvelous idea. I gladly accept.”


End file.
